Supramolecular self-assembly and reversible switching has been demonstrated for the first time between monovalent and multivalent carbohydrate ligands and the multivalency effect on lectin binding has been investigated. The self-assembly process is mediated through noncovalent interactions between pendant moieties on a polymer scaffold and a monosaccharide-functionalized viologen with cucurbit-[8]uril (CB[8]) acting as a "supramolecular handcuff". The rate of binding of the tetrameric lectin Concanavalin A (Con A) to a mannose-containing supramolecular glycopolymer was investigated through a standard turbidimetric assay.